Properties of singlet- and triplet-excited states of hemicyanine dyes
-
Daniel Mártire
,
Walter Massad
Abstract
The fluorescence emission spectra and fluorescence quantum yields of hemicyanine dyes LDS 698, LDS 722, and LDS 730 were measured in different media. No transient species was detected in the laser flash-photolysis experiments performed with Ar-saturated solutions of the dyes in methanol. However, in the presence of 0.08 M potassium iodide, the absorption of the triplet states was clearly observed. Oxygen consumption measurements in the absence and presence of a chemical trap (furfuryl alcohol) in MeOH: H2O (φ r = 1: 1) solutions of the dyes containing KI confirmed the generation of singlet molecular oxygen.
[1] Ashwell, G. J., Tyrrell, W. D., & Whittam, A. J. (2004). Molecular rectification: Self-assembled monolayers in which donor-(π-bridge)-acceptor moieties are centrally located and symmetrically coupled to both gold electrodes. Journal of the American Chemical Society, 126, 7102–7110. DOI: 10.1021/ja049633u. http://dx.doi.org/10.1021/ja049633u10.1021/ja049633uSearch in Google Scholar
[2] Cao, X., Tolbert, R. W., McHale, J. L., & Edwards, W. D. (1998). Theoretical study of solvent effects on the intramolecular charge transfer of a hemicyanine dye. The Journal of Physical Chemistry A, 102, 2739–2748. DOI: 10.1021/jp972190e. http://dx.doi.org/10.1021/jp972190e10.1021/jp972190eSearch in Google Scholar
[3] Cerdán, L., Costela, A., García-Moreno, I., Bañuelos, J., & López-Arbeloa, I. (2012). Singular laser behavior of hemicyanine dyes: unsurpassed efficiency and finely structured spectrum in the near-IR region. Laser Physics Letters, 9, 426–433. DOI: 10.7452/lapl.201210019. http://dx.doi.org/10.7452/lapl.20121001910.7452/lapl.201210019Search in Google Scholar
[4] Chmyrov, A., Sandén, T., & Widengren, J. (2010). Iodide as a fluorescence quencher and promoters: Mechanisms and possible implications. The Journal of Physical Chemistry B, 114, 11282–11291. DOI: 10.1021/jp103837f. http://dx.doi.org/10.1021/jp103837f10.1021/jp103837fSearch in Google Scholar
[5] Criado, S., Bertolotti, S. G., Soltermann, A. T., & García, N. A. (1997). Kinetics studies on the photosensitized oxidation (O2(1Δg)-mediated) of tryptophan-alkyl esters in Triton X-100 micellar solutions. Journal of Photochemistry and Photobiology B: Biology, 38, 107–113. DOI: 10.1016/s1011-1344(96)07447-7. http://dx.doi.org/10.1016/S1011-1344(96)07447-710.1016/S1011-1344(96)07447-7Search in Google Scholar
[6] Fromherz, P., & Heilemann, A. (1992). Twisted internal charge transfer in (aminophenyl)pyridinium. The Journal of Physical Chemistry, 96, 6864–6866. DOI: 10.1021/j100196a004. http://dx.doi.org/10.1021/j100196a00410.1021/j100196a004Search in Google Scholar
[7] García-Moreno, I., Costela, A., Martin, V., Pintado-Sierra, M., & Sastre, R. (2009). Materials for a reliable solid-state dye laser at the red spectral edge. Advanced Functional Materials, 19, 2547–2552. DOI: 10.1002/adfm.200900112. http://dx.doi.org/10.1002/adfm.20090011210.1002/adfm.200900112Search in Google Scholar
[8] Görner, H., & Gruen, H. (1985). Photophysical properties of quaternary salts of 4-dialkylamino-4′-azastilbenes and their quinolinium analogues in solution: IX. Journal of Photochemistry, 28, 329–350. DOI: 10.1016/0047-2670(85)85036-x. http://dx.doi.org/10.1016/0047-2670(85)85036-X10.1016/0047-2670(85)85036-XSearch in Google Scholar
[9] Kim, J. H., & Lee, M. Y. (1999). Excited-state photophysics and dynamics of a hemicyanine dye in AOT reverse micelles. The Journal of Physical Chemistry A, 103, 3378–3382. DOI: 10.1021/jp984167e. http://dx.doi.org/10.1021/jp984167e10.1021/jp984167eSearch in Google Scholar
[10] Mishra, A., & Haram, N. S. (2004). New push-pull type dendritic stilbazolium dyes: synthesis, photophysical and electrochemical investigation. Dyes and Pigments, 63, 191–202. DOI: 10.1016/j.dyepig.2004.02.011. http://dx.doi.org/10.1016/j.dyepig.2004.02.01110.1016/j.dyepig.2004.02.011Search in Google Scholar
[11] Qin, C. X., Tang, R. C., Chen, B., Chen, D. W., Wang, X. M., & Chen, G. Q. (2010). Study on the dyeing properties of hemicyanine dyes. I. Acrylic fabrics. Fibers and Polymers, 11, 193–198. DOI: 10.1007/s12221-010-0193-7. http://dx.doi.org/10.1007/s12221-010-0193-710.1007/s12221-010-0193-7Search in Google Scholar
[12] Sczepan, M., Rettig, W., Tolmachev, A. I., & Kurdyukov, V. V. (2001). The role of internal twisting in the photophysics of stilbazolium dyes. Physical Chemistry Chemical Physics, 3, 3555–3561. DOI: 10.1039/b102779b. http://dx.doi.org/10.1039/b102779b10.1039/b102779bSearch in Google Scholar
[13] Shim, T. K., Kim, D. S., Lee, M. H., Rhee, B. K., Cheong, H. M., Kim, H. S., & Yoon, K. B. (2006). Determination of the hyperpolarizability components of hemicyanine dyes by measuring the anisotropic fluorescence and second harmonic of the dyes uniformly aligned within zeolite channels. The Journal of Physical Chemistry B, 110, 16874–16878. DOI: 10.1021/jp062859u. http://dx.doi.org/10.1021/jp062859u10.1021/jp062859uSearch in Google Scholar PubMed
[14] Strehmel, B., Seifert, H., & Rettig, W. (1997). Photophysical properties of fluorescence probes. 2. A model of multiple fluorescence for stilbazolium dyes studied by global analysis and quantum chemical calculations. The Journal of Physical Chemistry, 101, 2232–2243. DOI: 10.1021/jp962835v. http://dx.doi.org/10.1021/jp962835v10.1021/jp962835vSearch in Google Scholar
[15] Valeur, B. (2002). Molecular fluorescence: Principles and applications. Weinheim, Germany: Wiley-VCH. Search in Google Scholar
[16] Wilkinson, F., Helman, W. P., & Ross, A. B. (1993). Quantum yields for the photosensitized formation of the lowest electronically excited singlet state of molecular oxygen in solution. Journal of Physical and Chemical Reference Data, 22, 113–262. DOI: 10.1063/1.555934. http://dx.doi.org/10.1063/1.55593410.1063/1.555934Search in Google Scholar
[17] Wilkinson, F., Helman, W. P., & Ross, A. B. (1995). Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation. Journal of Physical and Chemical Reference Data, 24, 663–1021. DOI: 10.1063/1.555965. 10.1063/1.555965Search in Google Scholar
[18] Yamaguchi, A., Nakano, M., Nochi, K., Yamashita, T., Morita, K., & Teramae, N. (2006). Longitudinal diffusion behavior of hemicyanine dyes across phospholipid vesicle membranes as studied by second-harmonic generation and fluorescence spectroscopies. Analytical and Bioanalytical Chemistry, 386, 627–632. DOI: 10.1007/s00216-006-0470-x. http://dx.doi.org/10.1007/s00216-006-0470-x10.1007/s00216-006-0470-xSearch in Google Scholar PubMed
© 2014 Institute of Chemistry, Slovak Academy of Sciences
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Articles in the same Issue
- Recent advances in application of liquid-based micro-extraction: A review
- Determination of nitrites and nitrates in drinking water using capillary electrophoresis
- Comparison of digestion methods for determination of total phosphorus in river sediments
- Interdisciplinary study on pottery experimentally impregnated with wine
- Improvement in γ-decalactone production by Yarrowia sp. after genome shuffling
- Development of an effective extraction process for coenzyme Q10 from Artemia
- Effect of anions on the structure and catalytic properties of a La-doped Cu-Mn catalyst in the water-gas shift reaction
- Effect of apple pomace powder addition on farinographic properties of wheat dough and biscuits quality
- Influence of caffeine and temperature on corrosion-resistance of CoCrMo alloy
- Cetyltrimethylammonium bromide- and ethylene glycol-assisted preparation of mono-dispersed indium oxide nanoparticles using hydrothermal method
- Sol-gel synthesis, characterisation, and photocatalytic activity of porous spinel Co3O4 nanosheets
- Solvent-free synthesis of β-enamino ketones and esters catalysed by recyclable iron(III) triflate
- Potassium phthalimide-catalysed one-pot multi-component reaction for efficient synthesis of amino-benzochromenes in aqueous media
- Organocatalytic SOMO reactions of copper(I)-acetylide and alkylindium compounds with aldehydes
- Molecular modelling and quantitative structure-activity relationship studies of anatoxin-a and epibatidine derivatives with affinity to rodent nAChR receptors
- Efficient one-pot synthesis of 2-hydroxyethyl per-O-acetyl glycosides
- Properties of singlet- and triplet-excited states of hemicyanine dyes
